I’ve been crossdressing since the age of 3 or 4, but it wasn’t until December of 2008 that Gabrielle finally got her face. The picture above was taken a couple of weeks ago, on the one year anniversary of my first time in full makeup. It’s not my best head shot, but certainly displays a vast improvement from a year prior in terms of looking more feminine up close.

After a lifetime of keeping this aspect of my life a carefully guarded secret, it was around this time last year (add a couple of weeks) that I was finally (fully) out to my wife. It was that same time, after months of planning, that my first ever feminine makeup transformation took place. The fabulous Mrs. H. agreed to take care of business for me. With years of experience doing her own makeup, and very well, I was sure to look gorgeous when all was complete… or so I initially thought.

I remember sitting in the bathroom while my wife carefully applied the makeup. She had me positioned so that I could not watch the process in the mirror – wanting it to be a surprise until finished. For decades I had waited for this moment and it was finally happening. This kind of anticipation is something that only another crossdresser (who also happened to wait far too long) can truly understand.

Mrs. H. smiled and giggled at times while applying my makeup. The process was pretty amusing to her, and she rather enjoyed it. Foundation, eye shadow, eye liner, blush, lipstick… and the wait was over. After a lifetime of self-denial, it was time to face my feminine side in the mirror – the woman within that had been unfairly locked away all my life.

It is hard to find the proper words to describe how I felt after coming face to face with “Gabrielle” for the first time in the mirror. To quote the fictional, but wise character of Spock, “…having is not so pleasing a thing, after all, as wanting. It is not logical, but it is often true.” The context in which I use this quote differs from how it was used in the Star Trek episode “Amok Time”, but seems fitting in light of the great disappointment experienced that moment.

Although it felt good to finally be in full makeup as Gabrielle, I clearly looked like a man wearing makeup and not at all like the beautiful, feminine face that I mentally envisioned for so long. Most of the photos taken that day looked awful. My desire was to look as female as possible and not like a man wearing makeup. It was quite a let-down. I couldn’t help but wonder how much better I might have looked had this moment arrived many years sooner on a much younger face.

The following day, we gave it another try. Some lessons were learned and a slightly different approach was taken this time. It fell short of what I hoped for, but was a welcome improvement. My face looked more feminine and less rugged. Click the thumbnail to the right to see the first-ever photo as Gabrielle I shared online (originally published on January 1, 2009).

Unfortunately, I’ll never know how beautiful I might have looked as Gabrielle in my teens or twenties. Being genetically male, my face is aging as such. Thought it does not look terribly old by any means, it does look fairly rugged and quite male. If you’re a young crossdresser, closeted or not, I suggest you begin experimenting with makeup if you haven’t already. Younger faces have the potential to look more feminine, and of course that much more attractive.

The silver lining is that I’ve gotten better at doing my makeup over the past year. Like many before me, I discovered that sticking with it and refining technique can greatly improve the end result. My preferred style isn’t exactly a modern, trendy approach. I love thick, black eyeliner, darker eye shadows (applied in an 80′s-ish fashion), bold lipstick, and sometimes a little too much blush (thought it is unintentional with the occasional excess blush).

Coming up
In my next post, I’ll be revisiting my first-ever published photos as Gabrielle. It was just over one year ago that I first ventured online as my feminine-self. A couple of then and now comparison photos were taken to celebrate. I hope you’ll join me while I reminisce and look back at my first baby steps into the world as Gabrielle… if only via the internet in the beginning.

Share your experience
At what age did you first start wearing makeup? How did it turn out your first time? Did you have any help (from a friend, girlfriend, or wife) getting started? Do you follow the latest makeup trends or do your own thing? If you’re the mother, sister, wife or signicant other of a crossdresser, have you helped someone get started or perhaps still do their makeup for them? Please take a moment and share.

Getting all done up in full makeup is a pretty big investment on two fronts, or so it is for me. Makeup isn’t cheap, and it takes a lot of makeup to transform Gabe’s rugged man-face into the soft and feminine face of Gabrielle. It also requires significant time to get all that makeup properly spackled on and detailed just right. Therefore I have to plan ahead, making sure that I have enough makeup on hand and a window of opportunity available in my busy life.

Unlike many genetic women, applying makeup isn’t something I get to practice on a daily basis. Sometimes it doesn’t quite turn out right and there’s a price to pay.

Full makeup vs. makeup-lite
I’ll often just apply partial makeup or what I refer to as makeup-lite: some eyeliner, blush, eye shadow, and lipstick. Quickie partial makeup jobs don’t take long, and not much makeup is used up in the process. If I were about 15 or so years younger, this approach might be all I need to look good as Gabrielle. If I want to get out of the house or take photos however, it requires a lot more makeup and time necessary to apply it. The main reason is vanity. If I’m going to show myself to the world in photos or in person, I’d prefer not to look like a man wearing makeup, or at least minimize that as much as possible. The signs of aging and my troublesome “man-shadow” need to be properly covered.

I’m a bit embarrassed to admit exactly how much time is required to complete a full makeup job. My wife can do her face up nicely in just minutes. Gabrielle requires considerably more makeup though. In my own defense, I don’t exactly get as much practice as women do, therefore it is a skill that is developing very slowly.

With the investment of so much time and effort into makeup application (including the extra body shaving involved and doing my nails, etc.), I’d like to be able to show something for it. Taking photos to capture and remember the moment is always high on my list. Unfortunately, I’m often unaware of a bad makeup day until reviewing my photos. Oddly, I can’t always tell in the mirror first.

The cost of a bad makeup day
So what exactly is the cost of a bad makeup day for Gabrielle?

1) Time I can’t have back
Time is lost that might have been spent attending to responsibilities or simply relaxing. My life is a busy one. Hours of precious time lost to something that didn’t yield any returns really hurts.

2) Depleted makeup supply
I’m out that much more makeup after a bad makeup day. If the makeup doesn’t turn out well, it feels like supplies (and money) were wasted rather than utilized.

3) Nothing to show for the investment
There’ll be no new photos to share with the world. Regret and frustration fill the space that beautiful photographic memories should have.

It is cheating?
Being pretty slick with photo editing software, I could probably salvage some of the (bad-makeup) photos by touching up the problem areas. I already do color correction, fix up small problem areas, and remove blemishes and other minor unsightly marks in my photos. I’ve always done the same for photos of me in guy-mode, too. Although I’m capable of going a lot further, doing any major re-touching (on my appearance) feels like cheating to me. I prefer to show people what I looked like rather than what I tried to look like.

Photo: “bad day”
The picture up top was taken on my most recent bad makeup day. Photo after photo, nothing was turning out well. My face was the major problem area… it just didn’t look right. It didn’t look feminine enough. Subtle mistakes in the way I did my makeup caused some major problems. I tried changing the lighting, but it didn’t help. It was very upsetting – to end up with such an unproductive investment of my time. Shifting focus from trying to get a good photo of me, I instead took a few shots of how I felt. They of course, looked terribly ugly.

Applying some artistic stylization, the photo was made to appear as you see it. I like that word – “stylization”. When I fail look presentable on my own, I can always stylize the look of the photo. It’s an artistic way of masking problem areas. The stylized look is obvious and therefore not really much of a “lie”, or that’s how I feel about it. I can now say that I’ve simply chosen an artistic approach to the image, rather than explain that I looked terrible and needed to somehow remove or obscure as much detail as possible in order hide that fact.

When life gives you lemons…
I’m a firm believer in the phrase “when life gives you lemons, make lemonade.” This particular bad makeup day wasn’t a total loss. Although I did not achieve (photographically) what I set out to, I was able to re-purpose a couple photos for other things. There is also the photo in this post, titled “bad day”. I don’t like it, but I don’t hate it either. Insecure as I am in my own vanity, there is a certain artistic quality to the picture. The look of defeat was captured on my face. It’s real. That’a how I truly felt in the moment. Frustrated and tired, I was about to call it a night… a wasted night. However that one last photo turned into this reflection upon a bad makeup day – something quite trivial to most people, and yet very important to so many of us.

Does it happen to you, too?
I know genetic women have their share of bad hair days, but I don’t imagine bad makeup days happens often. How many other t-girls experience the same? I’m not the only transgendered perfectionist, but perhaps I am the least skilled with makeup application… for now, anyway.

While examining my face closely in the mirror last night, I took a good look at all my new scars. They weren’t there a year ago, but now I have several of them scattered about. Some are more noticeable than others but they all stand out like a sore thumb to me. What caused these battle scars and why the picture of Homer Simpson mowing his lawn in Marge’s Sunday dress?

My battle scars are the result of shaving with a bladed razor. I’ve always used an electric razor because I have sensitive skin, but when I started wearing makeup late last year, the electric razor just didn’t cut it anymore (pun intended). My facial hair grows in pretty thick so unless I want to look like Homer Simpson in a dress (with his trademark 5 O’clock shadow), I have to use a bladed razor. It takes several passes in multiple directions to get the closest shave possible. The process is painful and small chunks of skin are sometimes removed with the stubble.

Even the more expensive multi-bladed razors do a number on me, but I am trying for a closer shave than normal. Several layers of concealer and foundation need to be applied in order to hide the remaining hint of 5 O’clock shadow. Of course, this can’t be started until after the bleeding has stopped. A month ago or so my upper lip was cut so deep that it took almost an hour for the bleeding to stop. When I removed my makeup later that night, the bleeding started right back up. That left a pretty noticeable scar.

I am getting better at it now. Last time, I only ended up with a few slight micro-nicks. The trade off is that the shave was not as close, so I had to compensate by caking on more foundation. It worked, but up close it didn’t look very natural.

I’m not very happy about the relatively new permanent markings on my face. It’s hard enough to transform Gabe’s rugged man-face into Gabrielle’s soft, attractive, feminine face without these additional scars working against me. At least I’m getting a little better at it now. I hope to get a face lift some day soon. Maybe that will also help minimize the appearance of the scars… when I can actually afford a face lift. Donations for an aging t-girl, anyone? :)

I often tell other crossdressers that I look so different en femme, fully made up, that no one (who knows my man-side) would ever recognize me if they saw. To test this a little, I changed my work-place desktop wallpaper to a close-up of Gabrielle’s face. The photo above is of my dual wide screen 22″ monitors at work. Guess what people are saying…

Several co-workers have seen my new desktop wallpaper in the past two weeks, since changing it to my femme-face. I’ve caught a few of them starring at it (rather than making eye-contact) while talking to me. Oddly, no one has said a word so far. No one has asked who the image is, or smiled in a way that might indicate they know it’s me. I’ve gotten absolutely no comments on the wallpaper image at all.

I’m not quite sure what I’d say if asked. Several stories have run through my mind, from telling them it’s a random image I came across and liked enough to make my wallpaper, to explaining it is a friend of my wife’s (which is fairly true). It’s not a good idea to do this without having a good story worked out to satisfy questions, but I’ve not yet decided what to say should I be asked. I guess I’ll find out if/when that finally happens.

The biggest surprise to me is that no one has questioned why another woman’s face (who is not my wife) is displayed larger than life on my monitors. My co-workers have seen my wife enough to know what she looks like. Perhaps they do think it’s my wife’s face and that it just looks a little different because of the way the image has been processed. Hard to say.

For the record, it is not in my best interest to let people at work know about my feminine side. It might drastically alter the work dynamic between my co-workers and I. There is also a good chance I could find myself unemployed. I wouldn’t get fired for being a crossdresser or anything, it would likely be because I put the wrong cover sheet on my TPS reports or something. ;) That would look better on paper and harder to fight in court.

To the right you can see the photo uncropped and without the blue tint. I tinted it blue because it makes a more visually pleasing desktop wallpaper that way, or so it does for me. I prefer not to have busy wallpapers that make my desktop icons difficult to see in contrast.

If you’re a crossdresser who’s not “out” at work, have you tried anything similar? Perhaps you have a photo of your femme-side hung with your family photos on the wall or sitting on your desk. Or maybe you don’t dare display your softer side at work in any way. Tell me about it.

UPDATE June 21, 2009:
I had to remove the desktop image from my computer at work. Ironically, people weren’t commenting on the image until after I decided to finally write about it. No one recognized the image as me, but I was getting questioned by co-workers about having another woman’s image on my desktop rather than that of my wife’s. I told Mrs. H. about this and she asked that I remove the image, to which I had decided to in light of how people were reacting. She felt funny about people thinking that I might be admiring another woman and I was already getting uncomfortable explaining to people that it was another woman (not my wife). It was an interesting experiment, but I think the desktop location was a poor choice. It gave the wrong impression that I have eyes for another woman outside of my marriage.